Winter Haven Homes with Restaurant Community Features

Winter Haven Homes with Restaurant Community Features

Welcome to Winter Haven, a charming city located in Polk County, Florida. Known for its beautiful lakes, Winter Haven offers a unique blend of natural beauty and modern conveniences.

If you're looking for a home with restaurant community features, Winter Haven has plenty to offer. Imagine living in a community where you can enjoy delicious meals without having to leave the neighborhood. Whether you're in the mood for a casual dining experience or a gourmet meal, you'll find options to suit every taste.

Living in a home with restaurant community features not only provides convenience but also creates a sense of community. You can socialize with neighbors, host gatherings, or simply enjoy a night out without the hassle of driving to a restaurant.

In Winter Haven, you can experience the best of both worlds – a peaceful residential setting with easy access to dining options. From cozy cafes to upscale eateries, this city has something for everyone.

If you're searching for a home in Winter Haven with restaurant community features, let us help you find the perfect property to suit your lifestyle. Experience the convenience and camaraderie of living in a community where good food is just steps away.

Newest Winter Haven Homes with Restaurant Community Features

306 Eagle Pond Drive Unit 306, Winter Haven
$211,000
2 Beds ⋅ 2 Baths ⋅ Eagle Pond Condo SubDv. ⋅ 33884 Zip Code
Beautiful completely updated condo in the highly desirable gated community of Cypresswood Golf and Country Club. It features tile flooring throughout the whole condo, marble kitchen countertops with an extended breakfast island, new water heater, matching marble on both bathroom vanities, upgraded lighting fixtures/ceiling fans, interior laundry with washer and dryer, pond view, and so much more. The master bedroom features an en suite bathroom while both bedrooms have a walk-in-closet. Additional linen storage exists in the main bedroom and hallway, plus an additional outside storage closet with shelves. The Cypresswood community features an 18-hole championship golf course designed by Ron Garl, junior Olympic sized community pool, lighted tennis courts, clubhouse with a restaurant, event space and more. Minutes from Hwy 27 and the I-4 corridor, Winter Haven's chain-of-lakes for the water enthusiast, Legoland Fl Park and Resort, Bok Tower gardens, and a brand new Publix shopping center within 2 miles and much more. Centrally located between Orlando and Tampa. Schedule your private showing today.

306 Eagle Pond Drive Unit 306, Winter Haven
5288 Green Drive, Winter Haven
$314,000
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 01 SubDv. ⋅ 33884 Zip Code
Welcome to this spacious Biscayne floor plan in Lake Ashton, a gated 55+ GOLF community in Winter Haven in Central Florida! This solar-powered home offers over 1,800 sq. ft. of living space with 3 bedrooms, 2 baths, a 2-car garage, and an expanded outdoor living area. One bedroom is ideal as an office or den. The open-concept floor plan features living, dining, dinette and kitchen areas, with triple sliders and double sliders opening to a covered, screened lanai with privacy panels, newer ceiling fans and lighting, and tile flooring. The kitchen boasts granite countertops, upgraded appliances, tile backsplash, newer sink and select lower-cabinet pullouts. The private primary suite includes two walk-in closets, dual vanities, soaking tub, step-in shower with grab bar and linen closet. Additional features include luxury vinyl plank flooring, 2022 roof and water heater, 2022 solar panels and gutters, automatic garage screen, hurricane shutters, and a beautifully landscaped paver outdoor area. The washer and dryer, garage refrigerator and generator convey. Enjoy amenity rich living in the highly desirable Lake Ashton community!

5288 Green Drive, Winter Haven
575 Saint Andrews Road, Winter Haven
$286,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
Golf Course Living with Total Peace of Mind! Welcome to your worry-free oasis on the green. Nestled within this beautiful, gated community of Cypresswood Golf and Country Club, this beautifully maintained 2-bedroom, 2-bathroom golf-front home offers the perfect blend of active resort living and quiet tranquility. Imagine waking up, stepping onto your private patio, and sipping your morning coffee while looking out over pristine, rolling fairway. What truly sets this home apart is that every major expense has already been taken care of for you. You can move in with absolute confidence, knowing you won't have to worry about costly upgrades or repairs for years to come. Recent premium updates include: •Brand New HVAC System (2024): Brand new inside and out for peak energy efficiency. •New Roof & Structural Updates (2022): Completely replaced roof, overhang, and facia boards. •Total Peace of Mind (2021): The entire home was fully re-plumbed. •Modern Conveniences: Updated kitchen and bathroom fixtures, a new garage •Modern Conveniences: Updated kitchen and bathroom fixtures, a new garage door opener, a new garbage disposal, and upgraded GFCI outlets. Storage is never an issue with the massive 23x23 oversized garage—offering ample space for your vehicles, workshop, and of course, your golf cart. Opportunities in Cypresswood like this do not last long. Don’t wait to start living your dream golf-course lifestyle—call today to schedule your private showing!

575 Saint Andrews Road, Winter Haven
5344 Nicklaus Drive, Winter Haven
$310,000
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph I SubDv. ⋅ 33884 Zip Code
Home for Sale in Lake Ashton, a Florida Retirement Community with Two (2) Golf Courses, Resort Style Amenities and Planned Activities like Trivia, Bingo, Dances, Day Trips, Holiday Events and MORE! This 3 Bedroom and 2 Bath home with over 1,600 sq. ft. living area would be a great seasonal home. The furniture in this home is negotiable. The exterior of this home has paver drive and walk ways, mature and well maintained landscape with rock-scape and landscape edging, a screened entry at the Front Door, and a Covered Lanai, on the front of the home, which is large enough for chairs. An irrigation system provides water to the large and beautiful Palm tree and other mature landscape around the home. This seasonally occupied and well maintained home offers an Open and Spacious Split Floor Plan with NO CARPET ANYWHERE! The kitchen features SS appliances (oven-December 2022, refrigerator 2021), Corian countertops, Dinette area with Bay Windows, Step Up breakfast bar and closet pantry. New Anderson Windows have been installed in the Dining room, Primary Bedroom and Primary Bathroom. Laminate flooring is in each of the bedrooms. The Primary Suite has 2 large walk-in closets, His/Her comfort height vanities, a Water closet and Large walk-in shower. The washer/dryer in the laundry room will be included in the sale of this home. The outdoor living area offers a 26 x 10 rear screened lanai and large paver area that is great for grilling. The 2 car garage is equipped with a "Skeeter Beater" for privacy and enjoying the cool cross breeze! Lake Ashton that offers 2 clubhouses, indoor and outdoor heated pools, pickle ball, tennis courts, racquetball, basketball, fitness centers, movie theaters, craft room, media center, several private lakes, private boat ramp/slips and more!! Come and enjoy your retirement and carefree living in the beautiful gated and guarded community of Lake Ashton today!

5344 Nicklaus Drive, Winter Haven
1321 Oakmont Drive, Winter Haven
$424,900
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph Ii South SubDv. ⋅ 33884 Zip Code
** CDD Debt Balance PAID IN FULL, saving you thousands! **A new four-season Sunroom was completed in April 2026. It is glass-enclosed with a separate HVAC mini-split and has beautiful new flooring. This home offers amazing curb appeal, with new landscaping on every side of the house, including lush privacy plantings in the back. The St. Marks floor plan has 3 Bedrooms and 2 Baths, plus a Den, spacious Laundry Room and a Double-car Garage with designated Golf Cart Entry. With 2,069 sq.ft. living area in the original house PLUS an additional 243 sq.ft. living area in the Sunroom, this OPEN and SPACIOUS home is ideal for entertaining friends and family. The tile plank flooring that appears "wood like" flows thru the LR, Formal Dining, Foyer, Kitchen, Dinette, Den, Sunroom and Laundry Rooms -- adding a touch of class to this truly charming home! The voluminous ceilings are enhanced with the 8ft. door openings in the home. The kitchen is enhanced with Granite countertops, soft close drawers and cabinets with newer hardware, stainless steel appliances, tiled backsplash, step-up breakfast bar with pendant lights, and abundant countertop space for food prep and display. The Dinette area, which is adjacent to the kitchen, is accessible from the Sunroom and the Den. The spacious Owners Suite occupies the left wing of the home and is a private retreat featuring His/Her walk-in closets and its very own En-Suite bath area. The Primary Bath offers His/Her comfort height vanities with Granite countertop and Newer Cabinet Hardware, a Walk-in shower w/glass door enclosure and Large soaking tub. The triple glass block allows an abundance of natural light into the space. A "Barn-Like" door on a smooth track system separates the Primary Suite from the Primary Bath. It's stylish and practical. On the right side of this Split Floor Plan home are Bedrooms 2 and 3 and the Guest Bath. The Guest Bath has a comfort height vanity, Shower/tub combo and Newer Hardware on the Cabs. It's perfectly positioned between the Guest Bedrooms. The laundry room is well designed and is the passage from the garage into the home. The laundry room has additional shelving for your storage needs. Hosting a Game Night or Want to Cozy Up with a Good Book? The brand-new SUNROOM would be the ideal place! It's accessible thru the TRIPLE SLIDERS in the LR & DOUBLE SLIDERS in the Dinette. ADDITIONAL UPGRADES: Whole House Gutter System, Automatic Screen (Skeeter Beeter) on the Garage Door, Storm Door on the front door, Pull Down Attic Ladder, new window dressings throughout the home, Six-Filter Reverse Osmosis Water System added to the Kitchen sink, Updated Painting in Several Rooms and Cabinet Handles in the Kitchen and Bathrooms. Lake Ashton has (2) clubhouses, (2) Golf Courses, Planned Activities and Resort Style Amenities. Residents enjoy 2 Swimming Pools (one Indoor & one Outdoor), Movie Theater, Bowling Lanes, Card, Craft and Billiard Rooms, Fitness Rooms, Media Rooms, Indoor Racquetball, Indoor 1/2 Court Basketball, Pickle Ball Courts, Tennis Courts, Shuffleboard Courts, Eagles Nest (an Eatery), a Pro Shop and MORE! Lake Ashton is a beautiful 55 Plus Community in Florida closely located to Shopping, Restaurants, Entertainment and Medical Facilities. MAKE AN APPOINTMENT TODAY TOUR THIS BEAUTIFUL HOME.

1321 Oakmont Drive, Winter Haven
2801 Wingfoot Court, Winter Haven
$245,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Golf Villa SubDv. ⋅ 33884 Zip Code
BEAUTIFUL VILLA READY TO MOVE IN! A brand-new HVAC system (June 2026), along with new insulation throughout the attic. Features include cathedral ceilings, elegant detailed trimwork with decorative corner blocks throughout, new flooring, plantation shutters on the windows, and three sets of French doors. The upgraded kitchen features stainless steel appliances, double ovens, and a built-in pantry with pull-out shelves. A utility closet provides additional storage, and the interior laundry room includes a full-size washer and dryer. The primary bathroom features dual showers and two vanities with wood cabinetry, while the second bathroom includes a jetted bathtub and wood cabinet vanity. Both bathrooms also feature skylights. Golf course frontage and two outdoor patio areas, with one overlooking the 8th fairway, plus a second patio with concrete privacy walls. HOA fee includes roof replacement when needed, so you never have to worry about roof expenses. Cypresswood Country Club community offers golf, a Jr. Olympic-size pool, tennis courts, pickleball courts, a restaurant and bar, social events, live music three nights a week, and lush, well-maintained surroundings. Come take a look at this one!

2801 Wingfoot Court, Winter Haven
5325 Snead Drive, Winter Haven
$349,500
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 01 SubDv. ⋅ 33884 Zip Code
MOTIVATED SELLERS!!! Welcome to one of THE MOST DESIRABLE AND BEAUTIFUL 55+ GATED/GUARD community in Winter Haven, FL! LAKE ASHTON has great amenities for their residents to enjoy every day and feel in PARADISE. An enormous club house were events are held, two pools, dog park, golf course, bowling, movie theater, fitness center, restaurant, and more. There's also a 2nd clubhouse available for residents. This gorgeous well maintained home has MULTIPLE VALUABLE UPGRADES that the future owner would enjoy. Even the floor plan was updated in the KITCHEN making this home UNIQUE in the neighborhood! NEW ROOF was installed in 2024, DISHWASHER FEB 2026, REFRIGETATOR NOV 2025, and WATER HEATER 2021. Also ENJOY the BENEFIT of having WATER SOFTENER, A WATER PURIFIER SYSTEM IN THE KITCHEN and QUARTS COUNTER TOPS. For the outdoor living you have a SPACIOUS TILE FLOORING, SCREENED LANAI WITH FLORIDA GLASS FOR PRIVACY. ONE OF THE BEST FEATURES OF THIS PROPERTY IS THAT IT HAS PAID OFF SOLAR PANELS. WHAT ELSE YOU CAN ASK FOR? This helps with the electric bill cost. COME AND SEE THIS AMAZING HOME THAT WILL MAKE YOU FEEL IN PARADISE!

5325 Snead Drive, Winter Haven
508 Eagle Pond Drive Unit 508, Winter Haven
$159,500
2 Beds ⋅ 2 Baths ⋅ Eagle Pond Condo SubDv. ⋅ 33884 Zip Code
Great Price! A Pristine 2 bed/2 bath condominium, Conveniently located in Cypresswood Golf & Country Club, on Dundee Rd near HWY 27. 2026 UPDATES - BRAND NEW hot water heater, countertops throughout, dishwasher, microwave, disposal, kitchen faucet. 2 year old energy efficient AC. Featuring 9' Ceilings, Crown Molding, 2" Blinds and Ceiling Fans throughout. You will love the spacious kitchen with pantry & lots of counter space. Both bedrooms feature walk in closets. Ample amount of closet space plus an outside storage room & assigned parking. Cypresswood residents enjoy a resort and country club lifestyle! There's an 18 hole championship golf course with a Clubhouse that offers chef prepared meals & live music. Also open to the public. Additional owner amenities include Brand New tennis & pickleball courts, and a half Olympic size pool. Located just minutes from trendy downtown Winter Haven, convenient to Hwy 27 & I-4. Close to Legoland, Bok Tower, shopping, dining, hospital and medical facilities. Just 5 minutes to BRAND NEW Publix and ALDI grocery's, 7-11 gas station & McDonalds.

508 Eagle Pond Drive Unit 508, Winter Haven
4040 Palma Ceia Circle, Winter Haven
$749,000
3 Beds ⋅ 4 Baths ⋅ Cypresswood Palma Ceia SubDv. ⋅ 33884 Zip Code
Meticulously maintained and beautifully remodeled, this exceptional Palma Ceia residence in Cypresswood offers pond frontage, three private en-suite bedrooms, a dedicated office, a heated swimming pool, and incredible golf course views. The pavered driveway and walkways, manicured flower gardens, and a 2022 black metal roof set the stage for the impressive interior. Elevated ceilings, crown molding, waterproof Pergo flooring, stone counters, and plantation shutters are just a few of the home’s stunning features. At the heart of the home is a spacious great room featuring a natural gas fireplace with shiplap façade. Triple sliding glass doors, with new screens, create a seamless indoor-outdoor flow to the covered lanai and pool area while showcasing the outdoor views. The updated kitchen features quartz counters, an island with a prep sink and filtered water, a Kohler workstation sink, breakfast bar, stainless appliances, double ovens, gas range, Bosch dishwasher, and a spacious dinette overlooking the pool. A private office provides the perfect setting for working from home. Designed to give everyone their own space, the home offers three bedrooms with en-suite bathrooms. The primary suite includes pool access, a tray ceiling, two walk-in closets with built-in shelving, and a gorgeous remodeled bathroom featuring a six-foot freestanding soaking tub, glass-enclosed walk-in shower, dual vanities, and a water closet. The second bedroom includes an equally impressive en-suite bath with custom tile flooring, a granite counter, tub, and separate walk-in shower. Located at the rear of the home, the third en-suite bedroom is ideal for visiting guests and can be closed off with a pocket door for added privacy. Its bathroom offers a granite counter with dual sinks, a tub and shower combo, and a linen closet. An additional linen closet is located in the guest-wing hallway. The interior laundry room provides a closet pantry, storage closet, and convenient half bathroom. Florida living takes center stage outdoors with a screen-enclosed heated pool, expansive covered lanai, and a separate screened area for sunning. The peaceful setting overlooks the pond and third hole of the golf course, where a variety of birds and wildlife can be enjoyed daily. Meticulously designed gardens, window planter boxes and a pavered sitting area near the pond—ideal for a fire pit—complete this private outdoor oasis. The two-car garage features an epoxy floor, utility sink, storage closets, and overhead storage racks. Additional improvements and features include a 2026 installed gas water heater, a 26-gauge standing seam metal roof (2022) with a 40-year warranty, dual-zone air conditioning (2020), irrigation on separate meter, plantation shutters throughout, remote-controlled lanai lighting, pool safety fence, Ring cameras, rain gutters, and more. Located within the guarded Cypresswood community, this remarkable home combines thoughtful updates, exceptional care, abundant privacy, and a truly beautiful golf course and waterfront setting. Cypresswood Golf & Country Club features an 18-hole championship golf course, driving range, pro shop, jr. olympic pool, tennis & pickleball courts, an event venue, a sports pub and more. Located just minutes from shopping, medical facilities and downtown Winter Haven. Centrally located between Tampa and Orlando with easy commutes to airports and beaches. Come see what this magnificent home and community in Central FL has to offer!

4040 Palma Ceia Circle, Winter Haven
1105 Eagle Pond Drive Unit 1105, Winter Haven
$160,000
2 Beds ⋅ 2 Baths ⋅ Eagle Pond Condo SubDv. ⋅ 33884 Zip Code
Welcome to maintenance-free living nestled in the thriving community of Cypresswood Golf and Country Club that offers an unparalleled lifestyle and peace of mind with a 24-hour guard at the gated entrance, perfect for year-round living or a worry-free seasonal getaway. This second-floor condo boasts a world of comfort and convenience with 10' high ceilings, tons of storage in generously-sized walk-in closets that both bedrooms offer as well as additional linen storage in the hallway and primary bedroom that will keep your space organized and clutter-free effortlessly. Dive into relaxation and fun at the community pool or host gatherings, socialize with neighbors, or simply unwind in the inviting communal spaces of the clubhouse. The on-site restaurant offers convenient and flavorful dining options, perfect after a tennis or pickleball match on the community's courts or day of golf on Cypresswood's 18-hole championship course. The low monthly HOA fee includes all exterior maintenance, landscaping, pest control, trash collection, and the pool and tennis amenities. Residents also enjoy a discount on daily golf and annual memberships! Minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options. Schedule your private showing today, and make this lovely condominium yours.

1105 Eagle Pond Drive Unit 1105, Winter Haven
665 Broadmoor Circle, Winter Haven
$165,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Tennis Villas SubDv. ⋅ 33884 Zip Code
Virtually Staged. Welcome to effortless Florida living in the highly sought-after gated Cypress Wood Golf & Country Club! Perfectly positioned on the beautifully maintained 10th hole, this 2-bedroom, 2-bath villa offers over 1,100 square feet of comfortable living with no close rear neighbors—just breathtaking views of lush fairways, mature oak trees, and Florida wildlife. Inside, you’ll find a bright, open floor plan complete with a spacious Florida room, the perfect place to enjoy your morning coffee or unwind while taking in the peaceful golf course scenery. Offered fully furnished with quick occupancy available, this home is truly move-in ready. Beyond the entrance, experience the exceptional lifestyle that makes Cypress Wood one of Central Florida’s most desirable golf communities. Enter through a 24-hour guard gate and enjoy a scenic drive along beautifully landscaped, tree-lined streets surrounded by meticulously maintained grounds and natural beauty. Residents have access to outstanding amenities including an 18-hole championship golf course, clubhouse, restaurant, community pool, tennis courts, pickleball courts, and a vibrant social atmosphere. The HOA provides lawn maintenance and exterior upkeep, allowing you to spend more time enjoying everything this resort-style community has to offer. Conveniently located just minutes from LEGOLAND Florida Resort, shopping, dining, and everyday conveniences, with easy access to Highway 27 and I-4, offering an easy commute to both Orlando and Tampa. Whether you’re searching for a full-time residence, winter retreat, or investment opportunity, this villa offers the perfect blend of comfort, convenience, and carefree Florida living. Schedule your private showing today !

665 Broadmoor Circle, Winter Haven
3158 Beauchamp Court, Winter Haven
$484,900
4 Beds ⋅ 3 Baths ⋅ Cypresswood Plantations SubDv. ⋅ 33884 Zip Code
Located on a quiet cut-de-sac in the desirable Plantations part of the guard gated golfing community of Cypresswood Golf & Country Club, this 4BR/3BA beauty w/ more than 2500 sq ft has upgrades galore & is just what you've been looking for! The home has a fantastic open floor plan w/ split bedrooms, volume ceilings, crown molding, double pane windows, plantation shutters, arched entryways, & super stylish hickory scraped wood looking tile throughout! The lovely formal dining room w/ it's arched entrances flows nicely just off the foyer, while another arch entry leads straight ahead into the spacious great room w/ a tray ceiling & French doors leading to the inviting Florida room. The large eat-in-kitchen features beautiful custom maple cabinets w/ pull-outs, new quartz countertops & tile backsplash, a breakfast bar, soft accent lighting over the cabinets & it comes equipped w/ all of the upgraded appliances including a new stainless steel refrigerator, microwave & gas range, as well as a new kitchen sink & faucet! The quaint breakfast nook has a beautiful picture window that provides lots of natural light while you're enjoying the serene backyard views. The primary suite is huge & features a cozy sitting area w/ French doors leading to the Florida rm & there's an ornate barn door entrance leading into the primary bathroom complete w/ a garden tub, nicely tiled step-in shower, double sink vanity w/ quartz countertop & a walk-in closet. The 2nd & 3rd BR's are situated on the other side of the living areas for added privacy & they have a Jack-n-Jill bath between them that has a double sink vanity w/ quartz countertop as well as a tub & shower combo. The 4th BR is located just down the hall from the Primary bedroom making it a nice option for a nursery/small child's room or an office. It would also be a nice guest room w/ the 3rd bathroom conveniently located right beside it w/ quartz countertop & a step-in shower w/ a nice glass enclosure. The large Florida rm has lots of windows overlooking the landscaped back yard & it even has a wet bar complete w/ mini fridge, a wine fridge & of course ...quartz countertops making it the perfect spot for entertaining. Additional features include an inside laundry room, a double car garage, fairly new C/H/A, a whole house gas generator, a water softner/purificiation system, central vac, & there's even a fire pit in the back yard on this 1/3+ acre property tucked away in Cypresswood Golf & Country Club, with lots of community amenities including a 24 hour manned gated entrance, a community pool for you to enjoy & not have to maintain, plus there's pickleball courts, tennis courts, a large clubhouse w/ fitness center, restaurant, pro shop & surrounded by the lovely golf course! Close to shopping, restaurants, medical, the new Publix, Legoland & more & Conveniently located in the heart of Central Florida between Orlando & Tamps and not far from all of the major attractions. All measurements are approximate and all info should be confirmed by buyers.

3158 Beauchamp Court, Winter Haven
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